Crystal structure, Hirshfeld surface analysis and spectroscopic characterization of the di-enol tautomeric form of the compound 3,3'-[(2-sulf-an-yl-idene-1,3-di-thiole-4,5-di-yl)bis-(sulfane-di-yl)]bis-(pentane-2,4-dione)

Abstract

The reaction between [TBA]₂[Zn(dmit)₂] and 3-chloro-2,4-penta-nedione yielded single crystals of the title compound, (3E,3'E)-3,3'-[(2-sulfanylidene-1,3-dithiole-4,5-diyl)bis(sulfanediyl)]bis(4-hydroxypent-3-en-2-one), C₁₃H₁₄O₄S₅, after solvent evaporation. The title compound crystallizes in the triclinic space group P with two mol-ecules related by an inversion center present in the unit cell. The central thione ring moiety contains a carbon-carbon double bond covalently linked to two sulfoxide substituents located outside of the plane of the ring. The S-C-C-S torsion angles are -176.18 (8) and -0.54 (18)°. Intra-molecular hydrogen bonds occur within the two dione substituents (1.67-1.69 Å). Adjacent asymmetric units are linked by C-H⋯S (2.89-2.90 Å), S⋯S [3.569 (1) Å] and O⋯H [2.56-2.66 Å between non-stacked thione rings] short contacts.

Keywords: crystal structure; di­thio­les; non-innocent; redox state; tautomerism.